Skip to main content
SpringerLink
Log in

POPd/TBAB co-catalyzed Suzuki cross-coupling reaction of heteroaryl chlorides/bromides with 4-fluorophenylboronic acid in water

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

An organic solvent free and efficient heterogeneous synthesis for bridging heteroaryl halides and 4-fluorophenylboronic acid was studied in aqueous media according to the Suzuki cross-coupling protocol. High yields of heteroaryl-aryl fluorides were successfully obtained with: chloro-/bromo-substituted pyridine, thiophene, indole, and inzole in neat water using palladium phosphinous acid complexes (POPd)/tetrabutylammonium bromide (TBAB) as co-catalysts. A possible mechanism for the heterogeneous coupling reaction is proposed and discussed according to the function of the TBAB interphases. The notable properties of the reported method are highly co-catalytic activity, hetero-atom tolerance, simple separating procedure and little environmental disposal impact.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. M. Sharif, A. Maalik, S. Reimann, H. Feist, J. Iqbal, T. Patonay, A. Villinger, P. Langer, J. Fluorine Chem. 146, 19 (2013)

    Article  CAS  Google Scholar 

  2. M. Zhu, W.J. Fu, G.L. Zou, C. Xu, Z.Q. Wang, J. Fluorine Chem. 163, 23 (2014)

    Article  CAS  Google Scholar 

  3. K. Müller, ChemBioChem 5, 637 (2004)

    Article  Google Scholar 

  4. M. Shimizu, T. Hiyama, Angew. Chem. Int. Ed. 44, 214 (2005)

    Article  CAS  Google Scholar 

  5. T. Furuya, J.E. Klein, T. Ritter, Synthesis 11, 1804 (2010)

    Google Scholar 

  6. M. Döbele, S. Vanderheiden, N. Jung, S. Bräse, Angew. Chem. Int. Ed. 49, 5986 (2010)

    Article  Google Scholar 

  7. L. Keyes, A.D. Sun, J.A. Love, Eur. J. Org. Chem. 3985 (2011)

  8. H.J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 5, 637 (2004)

    Article  Google Scholar 

  9. S.M. Ametamey, M. Honer, P.A. Schubiger, Chem. Rev. 108, 1501 (2008)

    Article  CAS  Google Scholar 

  10. W.B. Yi, J.J. Ma, J.Q. Jiang, C. Cai, W. Zhang, J. Fluorine Chem. 157, 84 (2014)

    Article  CAS  Google Scholar 

  11. T. Nöel, T.J. Maimone, S.L. Buchwald, Angew. Chem. Int. Ed. 50, 8900 (2011)

    Article  Google Scholar 

  12. T.J. Maimone, P.J. Milner, T. Kinzel, Y. Zhang, M.K. Takase, S.L. Buchwald, J. Am. Chem. Soc. 133, 18106 (2011)

    Article  CAS  Google Scholar 

  13. Z.Q. Yua, Y.W. Lv, C.M. Yu, W.K. Su, Tetrahedron Lett. 54, 1261 (2013)

    Article  Google Scholar 

  14. K.K. Laali, V.J. Gettwert, J. Fluorine Chem. 107, 31 (2001)

    Article  CAS  Google Scholar 

  15. M.J. Brown, V. Gouverneur, Angew. Chem. Int. Ed. 48, 8610 (2009)

    Article  CAS  Google Scholar 

  16. J.W. Graskemper, B.J. Wang, L.L. Qin, K.D. Neumann, S.G. DiMagno, Org. Lett. 13, 3158 (2011)

    Article  CAS  Google Scholar 

  17. G. Sandford, J. Fluorine Chem. 128, 90 (2007)

    Article  CAS  Google Scholar 

  18. N. Miyaura, A. Suzuki, Chem. Rev. 95, 2457 (1995)

    Article  CAS  Google Scholar 

  19. A. Suzuki, J. Organomet. Chem. 576, 147 (1999)

    Article  CAS  Google Scholar 

  20. T. Fujita, N. Suzuki, T. Ichitsuka, J. Ichikawa, J. Fluorine Chem. 155, 97 (2013)

    Article  CAS  Google Scholar 

  21. Q.P. Ding, H.F. Ji, D. Wang, Y.Q. Lin, W.H. Yu, Y.Y. Peng, J. Organomet. Chem. 711, 62 (2012)

    Article  CAS  Google Scholar 

  22. B. Li, C.P. Wang, G. Chen, Z.Q. Zhang, J. Environ. Sci. 6, 1083 (2013)

    Article  Google Scholar 

  23. G.Y. Li, J. Org. Chem. 67, 3643 (2002)

    Article  CAS  Google Scholar 

  24. C. Wolf, K. Ekoue-Kovi, Eur. J. Org. Chem. 1917 (2006)

  25. S.P. Khanapure, D.S. Garvey, Tetrahedron Lett. 45, 5283 (2004)

    Article  CAS  Google Scholar 

  26. T. Okazaki, K.K. Laali, S.D. Bunge, S.K. Adas, Eur. J. Org. Chem. 1630 (2014)

  27. C. Peng, G.B. Yan, Y. Wang, Y.B. Jiang, Y. Zhang, J.B. Wan, Synthesis 24, 4154 (2010)

    Google Scholar 

  28. R.B. De Vasher, L.R. Moore, K.H. Shaughnessy, J. Org. Chem. 69, 7919 (2004)

    Article  Google Scholar 

  29. A. Arcadi, G. Cerichelli, M. Chiarini, M. Correa, D. Zorzan, Eur. J. Org. Chem. 4080 (2003)

  30. D. Badone, M. Baroni, R.I. Cardamone, A. Lelmini, U. Guzzi, J. Org. Chem. 62, 7170 (1997)

    Article  CAS  Google Scholar 

  31. J.C. Bussolari, D.C. Rehborn, Org. Lett. 1, 965 (1999)

    Article  CAS  Google Scholar 

  32. R.B. Bedford, M.E. Blake, C.P. Butts, D. Holder, Chem. Commun. 466 (2003)

Download references

Acknowledgments

We are grateful for financial support from the Program for Liaoning Excellent Talents in University (No.LR2014009), (No.L2015258) and the kind donation of Pd-catalysts from Combiphos Catalysts.

Author information

Authors and Affiliations

  1. School of Chemical Engineering, University of Science and Technology Liaoning, Anshan, 114051, China

    Ben Li & Zhiqiang Zhang

Authors
  1. Ben Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhiqiang Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhiqiang Zhang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, B., Zhang, Z. POPd/TBAB co-catalyzed Suzuki cross-coupling reaction of heteroaryl chlorides/bromides with 4-fluorophenylboronic acid in water. J IRAN CHEM SOC 13, 637–644 (2016). https://doi.org/10.1007/s13738-015-0775-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-015-0775-9

Keywords

Search

Navigation